Information processing systems, information processing apparatus, and information processing methods

An information processing apparatus includes a communicator for communicating with an on-vehicle communicator mounted on a vehicle and a communication terminal to be operated by a user, and a controller configured to acquire, from the on-vehicle communicator, an update history of at least some of map data stored in a storage medium of the vehicle, determine whether the map data needs to be updated on a basis of the update history, transmit an inquiry signal to the communication terminal via the communicator to inquire whether to allow updating of the map data when the controller has determined to need to update the map data, and transmit an update instruction signal for instructing updating of the map data to the on-vehicle communicator via the communicator when the controller has received an allowance signal for permitting updating of the map data from the communication terminal via the communicator.